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Transformations of Ferric Chloride‐Generated Stilbene Cation Radicals. The Effect of Aromatic Substitution and a Comparison with Anodic Oxidation
Author(s) -
Hong FongJiao,
Chong KamWeng,
Low YunYee,
Thomas Noel F.,
Kam TohSeok
Publication year - 2015
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201500488
Subject(s) - chemistry , substituent , radical , reactivity (psychology) , ferric , medicinal chemistry , chloride , ring (chemistry) , radical nucleophilic aromatic substitution , anodic oxidation , organic chemistry , nucleophilic aromatic substitution , photochemistry , anode , nucleophilic substitution , electrode , medicine , alternative medicine , pathology
A systematic study on the FeCl 3 ‐induced oxidation of 1,2‐diarylalkenes was carried out with the focus on the variation of product type as a function of aromatic substitution, as well as to compare the reactivity of stilbene cation radicals generated via Fe III oxidation with those generated by anodic oxidation. The aromatic substituents were found to fall into three main categories, namely those that give rise to tetralins and/or dehydrotetralins, those that give products possessing pallidol and ampelopsin F‐type carbon skeletons, and last, those that give rise to trimeric products, indanes, and dehydrotetralins/tetralins. The latter are those stilbenes with a para ‐methoxy substituent in one ring and a para ‐ or meta ‐EWG (CF 3 , NO 2 , Cl, F) in the other, and represent the most prominent departure when compared with the behavior of the same stilbenes under the conditions of anodic oxidation. Reaction pathways to rationalize the formation of the different products are presented.